Pyridine → 1-Chloro-1-(4-methoxyphenyl)-1-trifluoromethylethane
Reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1)(O)[CH3:4].N1C=CC=CC=1.S(Cl)([Cl:25])(=O)=O>C1(C)C=CC=CC=1.CCOC(C)=O>[Cl:25][C:3]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1)([CH3:4])[C:2]([F:15])([F:14])[F:1]Participants
6
Conditions
- Temperature
- 55 °C
Procedure
A solution of 1,1,1-trifluoro-2-(4-methoxyphenyl)propan-2-ol (22.5 g, 102 mmol) in 150 ml of anhydrous toluene was treated sequentially with pyridine (8.26 ml, 102 mmol) and dropwise sulfuryl dichloride (11.2 ml, 153 mmol) at 0° C. The resulting mixture was then heated at 55° C. for 18 h. The reaction was diluted with 100 ml of EtOAc, washed with 100 ml of H2O and 100 ml of 1N HCl, dried over Na2SO4, and concentrated to give an oil which was filtered through a silica gel pad eluting with 0-5% EtOAc in hexanes to afford the title compound.
Workup
- washwashed with 100 ml of H2O and 100 ml of 1N HCl
- dry with materialdried over Na2SO4
- concentrationconcentrated
- customto give an oil which
- filtrationwas filtered through a silica gel pad
- washeluting with 0-5% EtOAc in hexanes
Sources & evidence
- ORD record
- ord-629d33aa62ba4bd1a93fbeb12433594a
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08633315B2
Reaction notes
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